CN109643765A - Charge-transporting material, printing ink composition and organic electronic element - Google Patents
Charge-transporting material, printing ink composition and organic electronic element Download PDFInfo
- Publication number
- CN109643765A CN109643765A CN201780051373.3A CN201780051373A CN109643765A CN 109643765 A CN109643765 A CN 109643765A CN 201780051373 A CN201780051373 A CN 201780051373A CN 109643765 A CN109643765 A CN 109643765A
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- organic
- hole transport
- group
- transport ability
- charge
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- 239000000463 material Substances 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims description 41
- 238000007639 printing Methods 0.000 title claims description 40
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- 230000005525 hole transport Effects 0.000 claims description 136
- 239000012044 organic layer Substances 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 29
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
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- 238000012545 processing Methods 0.000 claims description 8
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- 125000004429 atom Chemical group 0.000 claims description 4
- 210000002858 crystal cell Anatomy 0.000 claims description 4
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- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- JUHDUIDUEUEQND-UHFFFAOYSA-N methylium Chemical group [CH3+] JUHDUIDUEUEQND-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- NBJFDNVXVFBQDX-UHFFFAOYSA-I molybdenum pentafluoride Chemical compound F[Mo](F)(F)(F)F NBJFDNVXVFBQDX-UHFFFAOYSA-I 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 1
- 229940017144 n-butyl lactate Drugs 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- YHBDIEWMOMLKOO-UHFFFAOYSA-I pentachloroniobium Chemical compound Cl[Nb](Cl)(Cl)(Cl)Cl YHBDIEWMOMLKOO-UHFFFAOYSA-I 0.000 description 1
- AOLPZAHRYHXPLR-UHFFFAOYSA-I pentafluoroniobium Chemical compound F[Nb](F)(F)(F)F AOLPZAHRYHXPLR-UHFFFAOYSA-I 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- OEIMLTQPLAGXMX-UHFFFAOYSA-I tantalum(v) chloride Chemical compound Cl[Ta](Cl)(Cl)(Cl)Cl OEIMLTQPLAGXMX-UHFFFAOYSA-I 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
- H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
- C08G2261/3162—Arylamines
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/411—Suzuki reactions
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/95—Use in organic luminescent diodes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
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- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Liquid Crystal (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photovoltaic Devices (AREA)
Abstract
一个实施方式涉及一种电荷传输性材料，其含有具有下述式(Ia)所示的基团的空穴传输性聚合物和质子给予体。
One embodiment relates to a charge-transporting material comprising a hole-transporting polymer having a group represented by the following formula (Ia) and a proton donor.
Description
Technical field
This disclosure relates to charge-transporting material, printing ink composition, organic layer, organic electronic element, organic electroluminescent
Element (organic EL element), display element, lighting device and display device and organic layer, organic electronic element and Organic Electricity
The manufacturing method of electroluminescent element.
Background technique
Organic electronic element is the element that electronic work is carried out using organic matter, and expectation can play energy conservation, low price, flexibility
Etc. specialities, as replacing the technology of the previous inorganic semiconductor based on silicon to be concerned.
As the example of organic electronic element, organic EL element, organic photoelectric converter, organic transistor can be enumerated
Deng.
In organic electronic element, substitute of the organic EL element for example as incandescent lamp, gas-filled lamp etc. is solid as large area
State light source application is concerned.In addition, most having as the liquid crystal display (LCD) in replacement field flat-panel monitor (FPD)
The self-emitting display of power is also concerned, and commercialization is developed.
Organic EL element is roughly divided into low molecule type organic EL element and polymer electrolyte according to used organic material
Organic EL element both.In polymer electrolyte organic EL element, high molecular material is used as organic material；Low molecule type is organic
In EL element, low molecule material is used.Polymer electrolyte organic EL element and the low molecule mainly to form a film in vacuum systems
Type organic EL element is compared, and the simple film forming implemented using wet process such as printings is able to carry out, it is therefore contemplated that becoming to up to the present
Integral element for big picture organic el display afterwards.
On the other hand, it in organic EL element, in order to improve the element characteristics such as service life, luminous efficiency, carries out constituting element
The multiple stratification of organic layer.It, can be easily by being deposited while successively changing used compound in vapour deposition method
Realize multiple stratification.But it in order to use wet process to carry out multiple stratification to organic layer, needs molten in formation upper layer Shi Bushi lower layer
The method of solution.Then, it as being used to form the material of lower layer, such as has inquired into the compound with polymerizable group and (such as has joined
According to patent document 1).
Existing technical literature
Patent document
Patent document 1: Japanese Unexamined Patent Publication 2006-279007 bulletin
Summary of the invention
Technical problems to be solved by the inivention
The disclosure provides the charge-transporting material that can be become easy using the multiple stratification of the organic layer of wet process
And printing ink composition and the organic layer for having used them.In addition, the disclosure provides the organic layer with excellent solvent resistance
Organic electronic element and organic EL element and the display element, lighting device and display device for having used these elements.Into
And the disclosure provides the easy manufacturing method of organic layer, organic electronic element and organic EL element.
For solving the means of technical problem
It is exemplified below the example of embodiment.The present invention is not limited to the following embodiments and the accompanying drawings.
One embodiment is related to a kind of charge-transporting material, contains the sky with group shown in following formula (Ia)
Cave transporting polymer and proton donor.
[chemical formula number 1]
(in formula (Ia), A indicates that the organic group of monovalence, R indicate that the substituent group of monovalence, m indicate that 1~3 integer, n indicate
0~4 integer, m+n are 5 or less.)
In a preferred embodiment, group shown in the formula (Ia) contains group shown in following formula (Ib).
[chemical formula number 2]
(in formula (Ib), A indicates that the organic group of monovalence, R indicate that the substituent group of monovalence, n indicate 0~4 integer.)
In a preferred embodiment, the proton donor contains following formula (II) compounds represented.
[chemical formula number 3]
(in formula (II), Ra~RcHydrogen atom, alkyl, aryl alkyl, aryl or heteroaryl are each independently represented, is selected from
Ra~RcIn at least two group can also be mutually bonded to form ring.
A indicates anion.)
In a preferred embodiment, the hole transport ability polymer has branched structure.
In a preferred embodiment, the hole transport ability polymer, which has, is selected from aromatic amine structure and carbazole knot
It is at least one kind of in structure.
Additionally, it is preferred that an embodiment in, the hole transport ability polymer at least one end have the formula
(Ia) group shown in.
Another embodiment is related to a kind of printing ink composition, contain any among the above charge-transporting material and
Solvent.
Another embodiment is related to a kind of organic layer, is formed using charge-transporting material any among the above.
In addition, yet another embodiment is related to the organic electronic element with the organic layer；And there is the organic layer
Organic electroluminescent device.
In addition, yet another embodiment is related to the display element for having the organic electroluminescent device again；Have described
The lighting device of organic electroluminescent device；And has the display dress of the lighting device and the liquid crystal cell as display means
It sets.
In turn, and yet another embodiment is related to a kind of manufacturing method of organic layer, it includes: it is coated with the ink combination
Object, the process for forming coating layer；Apply at least one kind of processing in heat treatment and photo-irradiation treatment with to the coating layer
Process；A kind of manufacturing method of organic electronic element, it includes: the process for being coated with the printing ink composition, forming coating layer；
With the process for applying at least one kind of processing in heat treatment and photo-irradiation treatment to the coating layer, forming organic layer；With
And a kind of manufacturing method of organic electroluminescent device, it includes: the process for being coated with the printing ink composition, forming coating layer；
With the process for applying at least one kind of processing in heat treatment and photo-irradiation treatment to the coating layer, forming organic layer.
The present invention is related to the theme of Japanese Patent Application 2016-164723 record filed on August 25th, 2016, disclosure
Content is by referring to being incorporated herein.
Invention effect
According to the disclosure, it is possible to provide can be transmitted using the charge that the multiple stratification of the organic layer of wet process becomes easy
Property material and printing ink composition and the organic layer for having used them.In addition, according to the disclosure, it is possible to provide have solvent resistance
The organic electronic element and organic EL element of excellent organic layer and the display element of these elements, lighting device are used
And display device.In turn, according to the disclosure, it is possible to provide the easy manufacturer of organic layer, organic electronic element and organic EL element
Method.
Detailed description of the invention
Fig. 1 is the schematic cross-section for indicating an example of organic EL element of an embodiment.
Specific embodiment
Illustrate embodiments of the present invention below.The present invention is not limited to the following embodiments and the accompanying drawings.
The present inventors has made intensive studies, as a result, it has been found that, by using containing with the oxygen methylene for being bonded to phenyl ring
The hole transport ability polymer of base (benzyl ehter bond) and the charge-transporting material of proton donor, so that hole transport ability polymerize
The solubility of object changes, it is possible thereby to the solvent resistance of organic layer be improved, so as to complete this hair comprising various embodiments
It is bright.
< charge-transporting material >
According to one embodiment, it is poly- to contain the hole transport ability with group shown in formula (Ia) for charge-transporting material
Close object (being simply referred to as " hole transport ability polymer " sometimes below) and proton donor.Charge-transporting material can contain only a kind
Hole transport ability polymer, or two or more can be contained.It is given in addition, charge-transporting material can contain only 1 proton
Body, or two or more can be contained.
[hole transport ability polymer]
Hole transport ability polymer has group shown in following formula (Ia).By in the presence of proton donor to sky
Cave transporting polymer carries out heat treatment and/or photo-irradiation treatment, thus it is possible to vary hole transport ability polymer is in organic solvent
In solubility.
[chemical formula number 4]
In formula (Ia), A indicates that the organic group of monovalence, R indicate that the substituent group of monovalence, m indicate that 1~3 integer, n indicate 0
~4 integer, m+n are 5 or less." * " is to indicate the number at bonding position with the position that is bonded of other structures, m.N indicates of R
Number.R is preferably each independently the substituent group of monovalence, when R there are it is multiple when, multiple R can be identical also different each other.
Hole transport ability polymer preferably has group shown in following formula (Ib).Hole transport ability polymer is by having
Group shown in formula (Ib) can change well the solubility of hole transport ability polymer in organic solvent with efficiency.In addition,
Hole transport ability polymer group shown in end has formula (Ib) is preferred synthesis is easy.Formula (Ib)
Shown in group be in group shown in formula (Ia) m be 1 example.
[chemical formula number 5]
In formula (Ib), A indicates that the organic group of monovalence, R indicate that the substituent group of monovalence, n indicate 0~4 integer." * " table
Show and is bonded position with other structures.The number of n expression R.R preferably each independently represents the substituent group of monovalence, there are multiple by R
When, multiple R same to each other can also be different.
(group shown in formula (Ia))
In group shown in formula (Ia), A indicates organic group.As organic group, such as can enumerate substituted or unsubstituted
Aliphatic alkyl, substituted or unsubstituted aromatic hydrocarbyl and they be bonded made of alkyl.
The carbon number (not including the carbon containing number of substituent group) of aliphatic alkyl is 1 or more, in organic solvent from raising
Dissolubility from the perspective of, preferably 2 or more, more preferably 3 or more, further preferably 4 or more.In addition, aliphatic hydrocarbon
The carbon number (not including the carbon containing number of substituent group) of base is from can be readily available or synthesize for shown in introducing-type (Ia)
From the perspective of the reagent of group, preferably 22 or less, more preferably 12 or less, further preferably 8 or less.Aliphatic alkyl
For straight chain, branch or ring-type.As aliphatic alkyl, such as alkyl, alkenyl and alkynyl, preferably alkyl can be enumerated, as
Alkyl can enumerate methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, tert-butyl, amyl, hexyl, cyclohexyl, heptyl, pungent
Base, 2- ethylhexyl, nonyl, 3,7- dimethyl octyl, decyl, undecyl, dodecyl, tridecyl, myristyl, ten
Five alkyl, cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl (icosyl group), n-eicosane base
(eicosyl group) etc..
The carbon number (not including the carbon containing number of substituent group) of aromatic hydrocarbyl is 6 or more.In addition, the carbon of aromatic hydrocarbyl
Number (not including the carbon containing number of substituent group) from the viewpoint of improving dissolubility in organic solvent, preferably 30 with
Under, more preferably 14 or less, further preferably 10 or less.As aromatic hydrocarbyl, aryl can be enumerated, as aryl, can be lifted
Out phenyl, naphthalene, anthryl, naphthacene base, pentacene, phenanthryl,Base, triphenylene, benzo anthryl, pyrene base, dinaphthyl product
Phenyl, pentaphene base, perylene base, five helicene bases etc..
In alkyl made of substituted or unsubstituted aliphatic alkyl is bonded with substituted or unsubstituted aromatic hydrocarbyl,
" aliphatic alkyl " and " aromatic hydrocarbyl " is as described above.The carbon number (not including the carbon containing number of substituent group) of the alkyl is 7
More than.In addition, the carbon number (not including the carbon containing number of substituent group) of the alkyl is from improving in organic solvent deliquescent
Viewpoint is set out, and preferably 30 or less, more preferably 14 or less, further preferably 10 or less.As the alkyl, aryl can be enumerated
Alkyl and alkylaryl.As aryl alkyl, benzyl, phenethyl, naphthyl methyl, naphtylethyl group, diphenyl can be specifically enumerated
Methyl etc..As alkylaryl, tolyl, ethylphenyl, methyl naphthalene, ethyl naphthalene, xylyl etc. can be specifically enumerated.
R indicates the substituent group of monovalence, such as can enumerate aftermentioned-R1(but except the case where being hydrogen atom) ,-OR2、-
SR3、-OCOR4、-COOR5、-SiR6R7R8, halogen atom etc..N be 0~4 integer, preferably 0 or 1.When n is 2~4, R can phase
It is identical between mutually can also be different.
It is considered that by implementing heat treatment and/or light to hole transport ability polymer in the presence of proton donor
Treatment with irradiation, Oxymethylene cracking in group shown in formula (Ia), A-O- base is left away, so that the compatibility to organic solvent occurs
Variation.In group shown in formula (Ia), in case where m is 1, n is 0, reaction equation described below.Hole transport ability polymer
The variation of solubility be presumably due to a part of group shown in formula (Ia) and leave away and occur.To occur sometimes below from
The A-O- group gone is referred to as " atomic group (A) ".
[chemical formula number 6]
R in above-mentioned reaction equation indicates the polymer chain of hole transport ability polymer.
For example, being in hole when the group shown in formula (Ia) has atomic group (A) high to the compatibility of organic solvent
The high state of the solubility of transporting polymer in organic solvent.If atomic group (A) group shown in formula (Ia) is left away,
Then become the low state of the solubility of hole transport ability polymer in organic solvent.
By utilizing the variation, the charge-transporting material containing hole transport ability polymer for example can preferably be made
For organic electronic material carry out using.Specifically, dissolving the hole transport ability polymer with group shown in formula (Ia)
In organic solvent, coating layer is formed using rubbing method.Later, so that atomic group (A) is left away from hole transport ability polymer, make
Hole transport ability polymer reduces the solubility of organic solvent.Thus to obtain contain the hole low to the solubility of organic solvent
The organic layer of transporting polymer.Using gained organic layer as lower layer, by rubbing method formed upper layer when, lower layer can be inhibited to have
Dissolution in solvent can form upper layer well.It is poly- by using the hole transport ability with group shown in formula (Ia)
Object is closed, the multiple stratification of the organic layer carried out using wet process is become easy.
Group shown in formula (Ia) is for the reasons why reacting with aftermentioned proton donor is easy to, preferably at least by it
It is directed into 1 or more end of hole transport ability polymer.End refers to the end of polymer chain.
The number of group shown in formula (Ia) contained in 1 molecule of hole transport ability polymer is not particularly limited.In order to
Solubility is set to change, preferably 2 or more, more preferably 3 or more.In addition, from sufficient hole transport ability is ensured
Viewpoint is set out, and preferably 1,000 or less, more preferably 500 or less.
The ratio of group shown in formula (Ia) in hole transport ability polymer is from the dissolution for making hole transport ability polymer
From the perspective of degree changes, on the basis of entire infrastructure unit, preferably 5 moles of % or more, more preferably 10 moles of %
It above, is more preferably 15 moles of % or more.In addition, the ratio of group shown in formula (Ia) in hole transport ability polymer
From the viewpoint of reducing film thickness and reducing, preferably 95 moles of % or less, more preferably 90 moles of % or less, it is more preferably
85 moles of % or less.In addition, " ratio of group shown in formula (Ia) " here refers to the knot with group shown in formula (Ia)
The ratio of structure unit.
(structure of hole transport ability polymer)
Hole transport ability polymer can be straight-chain, or also can have branched structure.The hole of straight-chain passes
Defeated property polymer has 2 ends, and the hole transport ability polymer with branched structure has 3 or more ends.End is
Refer to the end of polymer chain.Make the changed viewpoint of the solubility of hole transport ability polymer and raising well from efficiency
From the perspective of the service life of organic electronic element, hole transport ability polymer preferably has branched structure.
The structural unit that hole transport ability polymer preferably comprises the ability with transporting holes (sometimes referred to as " has sky
The structural unit of cave transporting ").Hole transport ability polymer can be the condensate with a kind of structural unit, or can be with
It is the condensate with two or more structural unit.When hole transport ability polymer is copolymer, copolymer can be alternating, nothing
Rule, block or graft copolymer can also be that the copolymer of the intermediate structure with them, such as random with block are total to
Polymers.In one embodiment, structural unit refers to monomeric unit.
For example, hole transport ability polymer can be at least containing divalent structural units L and composition with hole transport ability
The monovalence structural unit T of terminal part, and further containing structural unit the B more than trivalent for constituting branch portion.That is, hole transport
Property polymer can be used as " structural unit with hole transport ability " at least have structural unit L, and then structural unit T and/
Or structural unit B is the structural unit with hole transport ability.In addition, for example hole transport ability polymer can also at least contain
The monovalence structural unit T of trivalent structural unit B and composition terminal part with hole transport ability, and further contain arbitrary two
Valence structural unit L.That is, hole transport ability polymer, which can be used as " structural unit with hole transport ability ", at least has structure
Unit B, and then structural unit T and/or structural unit L are the structural units with hole transport ability.Hole transport ability polymer
Can be containing each structural unit for being respectively only a kind, or respectively a variety of each structural units can also be contained.Hole transport
In property polymer, each structural unit is mutually bonded at the bonding position of " monovalence "~" more than trivalent " respectively.
Group shown in formula (Ia) contain structural unit L, structural unit T and structural unit B it is at least one kind of in.
From the viewpoint of efficiency changes solubility well, preferred structure unit T has group shown in formula (Ia).
As the example of part-structure contained by hole transport ability polymer, following example can be enumerated.Hole transport ability polymerization
Object is not limited to have following part-structure person.In part-structure, " L " indicate structural unit L, " T " indicate structural unit T,
" B " indicates structural unit B." * " expression is bonded position with other structures unit.In part-structure below, multiple L be can be
Mutual identical structural unit can also be mutual different structural unit.It is also same for T and B.
The hole transport ability polymer of straight-chain
[chemical formula number 7]
T-L-L-L-L-L-*
Hole transport ability polymer with branched structure
[chemical formula number 8]
(structural unit L)
Structural unit L is preferably the divalent structural units with hole transport ability.As long as preferred structural unit L contains
The atomic group of ability with transporting holes, is not particularly limited.For example, structural unit L be selected from it is substituted or unsubstituted,
Aromatic amine structure, carbazole structure, thiophene-structure, fluorene structured, benzene structure, biphenyl structural, triphen structure, naphthalene structure, anthracene structure,
Naphthacene structure, luxuriant and rich with fragrance structure, dihydro phenanthrene structure, pyridine structure, pyrazine structure, quinoline structure, isoquinoline structure, quinoxaline structure,
Acridine structure, phenanthroline structure, furan structure, pyrrole structure, oxazole structure, oxadiazoles structure, thiazole structure, thiadiazoles knot
Structure, triazole structure, benzothiophene structure, benzoxazoles structure, benzoxadiazole structure, benzothiazole structure, diazosulfide
Structure, benzotriazole structure and contain the one kind or two or more structure in them.Aromatic amine structure is preferably triarylamine
Structure, more preferably triphenylamine structure.
In one embodiment, structural unit L is preferably selected from substitution from the viewpoint of obtaining excellent hole transport ability
Or unsubstituted, aromatic amine structure, carbazole structure, thiophene-structure, fluorene structured, benzene structure and contain a kind or 2 kinds in them
Above structure is more preferably selected from substituted or unsubstituted, aromatic amine structure, carbazole structure and containing a kind or 2 in them
Kind or more structure.
As the concrete example of structural unit L, following example can be enumerated.Structural unit L is not limited to following example.
[chemical formula number 9]
[chemical formula number 10]
R each independently represents hydrogen atom or substituent group.It is preferred that R is each independently selected from-R1、-OR2、-SR3、-
OCOR4、-COOR5、-SiR6R7R8, halogen atom, group shown in group and following formula (Ic) shown in above-mentioned formula (Ib).R1~
R8Each independently represent hydrogen atom；Straight chain, ring-type or the branched alkyl that carbon number is 1~22；Or carbon number is 2~30
Aryl or heteroaryl.Aryl is the atomic group after removing 1 hydrogen atom in aromatic hydrocarbon.Heteroaryl is from heteroaromatic
Atomic group after removing 1 hydrogen atom.Alkyl can also further be replaced by carbon number for 2~30 aryl or heteroaryls, virtue
Base or heteroaryl can also further be replaced by straight chain, ring-type or branched alkyl that carbon number is 1~22.R be preferably hydrogen atom,
Alkyl, aryl, alkyl substituting aromatic base.Ar indicates that carbon number is 2~30 arlydene or inferior heteroaryls.Arlydene is from aromatic series
The atomic group after 2 hydrogen atoms is removed in hydrocarbon.Inferior heteroaryl is the atomic group after removing 2 hydrogen atoms in heteroaromatic.
Ar is preferably arlydene, more preferably phenylene.
[chemical formula number 11]
A is identical as the A in group shown in formula (Ia).
As aromatic hydrocarbon here, monocycle, fused rings or 2 or more in monocycle and fused rings can be enumerated
By polycyclic made of singly bound.As heteroaromatic, monocycle, fused rings can be enumerated or selected from monocycle and fused rings
In 2 above by polycyclic made of singly bound.It is also identical in aftermentioned fragrant three base and three base of heteroaryl.
(structural unit T)
Structural unit T is the monovalence structural unit for constituting the terminal part of hole transport ability polymer.Structural unit T has no spy
It does not limit, such as selected from substituted or unsubstituted, aromatic hydrocarbon structures, heteroaromatic structure and 1 in them can be contained
Kind or structure of more than two kinds.Structural unit T also can have structure identical with structural unit L.In one embodiment, knot
Structure unit T from the viewpoint of in the case where not reducing charge-transporting assign durability, it is preferably substituted or unsubstituted
Aromatic hydrocarbon structures, more preferably substituted or unsubstituted benzene structure.
As the concrete example of structural unit T, following example can be enumerated.Structural unit T is not limited to following example.
[chemical formula number 12]
R is identical as the R in structural unit L.Hole transport ability polymer terminal part have formula (Ia) shown in group when,
It is preferred that in R at least any one be group shown in group shown in above-mentioned formula (Ib) or formula (Ic).
(structural unit B)
Structural unit B is the structure for constituting the trivalent in branch portion or more when hole transport ability polymer has branched structure
Unit.Structural unit B preferably below sexavalence, is more preferably three from the viewpoint of the durability for improving organic electronic element
Valence or tetravalence.Structural unit B is preferably the unit with charge-transporting.For example, structural unit B from improve organic electronic element
Durability from the perspective of, be selected from substituted or unsubstituted, aromatic amine structure, carbazole structure, fused polycyclic aromatic series
Hydrocarbon structure and contain the one kind or two or more structure in them.
As the concrete example of structural unit B, following example can be enumerated.Structural unit B is not limited to following example.
[chemical formula number 13]
W indicates the linking group of trivalent, such as indicates that carbon number is 2~30 three bases of three base of virtue or heteroaryl.Fragrant three bases are
Atomic group after removing 3 hydrogen atoms in aromatic hydrocarbon.Three base of heteroaryl is after removing 3 hydrogen atoms in heteroaromatic
Atomic group.Ar each independently represents the linking group of divalent, such as each independently represents the arlydene that carbon number is 2~30
Or inferior heteroaryl.Ar is preferably arlydene, more preferably phenylene.Y indicates the linking group of divalent, such as can enumerate from structure
Into one in group in the R (but except group shown in the group of formula (Ib) and formula (Ic)) of unit L with 1 or more hydrogen atom
Step removes the bivalent group after 1 hydrogen atom.Z indicates any one of carbon atom, silicon atom or phosphorus atoms.Structural unit
In, phenyl ring and Ar can also have substituent group, as the example of substituent group, can enumerate the R in structural unit L.
(number-average molecular weight)
It is appropriate that the number-average molecular weight of hole transport ability polymer is considered that dissolubility, film forming in a solvent etc. come
Ground adjustment.Number-average molecular weight from the viewpoint of hole transport ability is excellent, preferably 500 or more, more preferably 1,000 or more,
Further preferably 2,000 or more.In addition, number-average molecular weight is from keeping good solubility in a solvent, make printing ink composition
Preparation become easy from the perspective of, preferably 1,000,000 or less, more preferably 100,000 or less, further preferably
50,000 or less.
(weight average molecular weight)
It is appropriate that the weight average molecular weight of hole transport ability polymer is considered that dissolubility, film forming in a solvent etc. come
Ground adjustment.Weight average molecular weight is from the viewpoint of hole transport ability is excellent, preferably 1,000 or more, more preferably 5,000 with
Above, further preferably 10,000 or more.In addition, weight average molecular weight is from keeping good solubility in a solvent, make ink group
Close object preparation become easy from the perspective of, preferably 1,000,000 or less, more preferably 700,000 or less, further it is excellent
It is selected as 400,000 or less.
Number-average molecular weight and weight average molecular weight can by gel permeation chromatography (GPC), use standard polystyren
Standard curve is measured.
(ratio of structural unit)
When hole transport ability polymer contains structural unit L, the ratio of structural unit L is from obtaining abundant hole transport ability
Viewpoint is set out, and on the basis of entire infrastructure unit, preferably 10 moles of % or more, is more preferably 20 moles of % or more, is further
Preferably 30 moles of % or more.In addition, the ratio of structural unit L is in view of structural unit T and the structure list imported as needed
When first B, preferably 95 moles of % or less, more preferably 90 moles of % or less, further preferably 85 moles of % or less.
The ratio of structural unit T contained by hole transport ability polymer from improve organic electronic element characteristic viewpoint or
Viscosity is inhibited to rise, from the perspective of the synthesis of progress hole transport ability polymer well, on the basis of entire infrastructure unit,
Preferably 5 moles of % or more, more preferably 10 moles of % or more, further preferably 15 moles of % or more.In addition, structural unit
The ratio of T from the viewpoint of obtaining abundant hole transport ability, preferably 60 moles of % or less, more preferably 55 moles of % with
Under, further preferably 50 moles of % or less.
Hole transport ability polymer is when end has group shown in formula (Ia), all ends of hole transport ability polymer
The ratio of structural unit with group shown in formula (Ia) in end is from the viewpoint of changing solubility fully, with whole
It is 25 moles of % or more, more preferably 30 moles of % or more, further preferably 35 moles of % or more on the basis of the number of end.On
Limit is not particularly limited, and is 100 moles of % or less.
When hole transport ability polymer contains structural unit B, the ratio of structural unit B is from improving the resistance to of organic electronic element
From the perspective of long property, on the basis of entire infrastructure unit, preferably 1 mole of % or more, more preferably 5 moles of % or more, into
One step is preferably 10 moles of % or more.In addition, the ratio of structural unit B improves from inhibition viscosity, carries out hole transport well
Property polymer synthesis viewpoint or from the perspective of obtaining sufficient hole transport ability, preferably 50 moles of % or less, more
Preferably 40 moles of % or less, further preferably 30 moles of % or less.
In view of hole transport ability, durability, productivity etc. balance when, hole transport ability polymer contains structural unit
When L and structural unit T, the ratio (molar ratio) of structural unit L and structural unit T be preferably L:T=100:1~70, more preferably
For 100:3~50, further preferably 100:5~30.In addition, when charge-transporting polymer further contains structural unit B,
The ratio (molar ratio) of structural unit L, structural unit T and structural unit B be preferably L:T:B=100:10~200:10~100,
More preferably 100:20~180:20~90, further preferably 100:40~160:30~80.
The ratio of structural unit can be used to synthesize and correspond to each structure list used in hole transport ability polymer
The input amount of the monomer of member acquires.In addition, the ratio of structural unit can use hole transport ability polymer1H NMR light
The signal integration value in each structural unit source in spectrum is found out as average value.Due to simple, when input amount understands, preferably
Using the value acquired using input amount.
(manufacturing method of hole transport ability polymer)
Hole transport ability polymer can use various synthetic methods and be manufactured, and be not particularly limited.For example, can make
With Suzuki coupling reaction, root bank coupling reaction, Sonogashira coupling reaction, Stille coupling reaction, Buchwald-
Coupling reaction well known to Hartwig coupling reaction etc..Suzuki coupling reaction refers in aromatic boric acid derivative and aromatic series halogen
Cause the reaction for having used the cross-coupling reaction of Pd catalyst between compound.It is desired by making according to Suzuki coupling reaction
Aromatic rings between be bonded, can easily manufacture hole transport ability polymer.
In coupling reaction, as catalyst, such as Pd (0) compound, Pd (II) compound, Ni compound etc. are used.Separately
Outside, it can also use using three (two benzylideneacetones) two palladiums (0), palladium acetate (II) etc. as precursor, by being mixed with phosphine dentate
And the catalyst kind generated.The synthetic method of hole transport ability polymer is for example referred to International Publication No. WO2010/
No. 140553 records.
[proton donor]
Proton donor refers to the compound that proton is given to charge-transporting polymer.Think group shown in formula (Ia)
By receiving giving for proton from proton donor, so that Oxymethylene cracks.As proton donor, such as can enumerate
The organic acids such as carboxylic acid, sulfonic acid, inorganic acid, salt etc..From the viewpoint of dissolubility in organic solvent, preferred salt.
As salt, using can be to the compound for the proton that charge-transporting polymer is given at least one.As
Salt, can Ju Chu phosphonium salt, oxonium salt, sulfonium salt, ammonium salt etc..From the viewpoint of electric conductivity raising, preferred ammonium salt.
Ammonium salt contains azonia.As azonia, NH4 can be enumerated+, primary azonia, secondary azonia and tertiary carbon
Cation.
As ammonium salt, following formula (II) compounds represented can be used.
[chemical formula number 14]
Ra~RcHydrogen atom, alkyl, aryl alkyl, aryl or heteroaryl are each independently represented, R is selected froma~RcIn
At least two group can be mutually bonded to form ring.
A indicates anion.
Think that formula (II) compound represented is contained in hole transport ability polymer with making in charge-transporting material
Oxymethylene cracking function and to both functions of the doping function of hole transport ability polymer.
From the viewpoint of improving dissolubility in organic solvent, preferably Ra~RcIn at least one be alkyl or aryl
Alkyl, more preferably alkyl.More preferable Ra~RcAll alkyl or aryl alkyl, particularly preferably alkyl.That is, it is preferred that Ra~
RcIt will not be all aryl and/or heteroaryl.
Alkyl can be any one of straight chain, branch or ring-type, can also have a substituent group, carbon number is preferably 1~24,
It more preferably 1~20, is more preferably 1~18.As concrete example, can enumerate methyl, ethyl, propyl, isopropyl, butyl,
Isobutyl group, tert-butyl, amyl, hexyl, cyclohexyl, heptyl, octyl, 2- ethylhexyl, nonyl, decyl, dodecyl, the tetradecane
Base, octadecyl, 3,7- dimethyl octyl, lauryl, trifluoromethyl, pentafluoroethyl group, perfluoro butyl, perfluoro hexyl, perfluor are pungent
Base etc..
From viewpoints, preferably R such as the dissolubilities improved in organic solventa~RcIn at least one be carbon number be 7 with
On alkyl, Ra~RcIn it is other at least one be carbon number be 6 alkyl below；More preferable Ra~RcIn 1 be carbon
Alkyl, R of the number for 7 or morea~RcIn other 2 be carbon number be 6 alkyl below.
Aryl also can have substituent group.The carbon number of the monovalence aryl of unsubstituted state is preferably 6~60, more preferably 6
~18.It specifically may be exemplified out phenyl, (C1~C12 indicates that the carbon number of substituent group is 1~12 to C1~C12 alkoxyl phenyl.With
Down similarly), C1~C12 alkyl phenyl, 1- naphthalene, 2- naphthalene, 1- anthryl, 2- anthryl, 9- anthryl, phenanthryl, pyrene base, two
Rylene base, pentafluorophenyl group etc., preferably C1~C12 alkoxyl phenyl or C1~C12 alkyl phenyl.
Heteroaryl also can have substituent group.The carbon number of the monovalence heteroaryl of unsubstituted state is preferably 4~60, more preferably
It is 4~20.It specifically may be exemplified out thienyl, C1~C12 alkylthrophene base, pyrrole radicals, furyl, pyridyl group, C1~C12
Alkylpyridyl etc., preferably thienyl, C1~C12 alkylthrophene base, pyridyl group or C1~C12 Alkylpyridyl.C1~C12
As described above.
Aryl alkyl is the group that at least one in hydrogen atom possessed by alkyl has been substituted with aryl.Aryl alkyl is also
There can be substituent group.The carbon number of the monovalence aryl alkyl of unsubstituted state is preferably 7~19, more preferably 7~13.As alkane
Base can exemplify aforesaid alkyl, as aryl, can exemplify aforesaid aryl.Benzyl, phenethyl, naphthalene can specifically be exemplified
Methyl, naphtylethyl group, diphenyl methyl etc..
A is anion, for example, can enumerate halide ion, hydroxide ion, azochlorosulfonate acid ion, sulfate ion, carbonate ions,
Phosphate ion, borate ion, anion in following formula (1b)~(5b) etc..Preferably yin shown in following formula (4b) from
Son.
[chemical formula number 15]
E1Indicate oxygen atom, E2Indicate nitrogen-atoms, E3Indicate carbon atom, E4Indicate boron atom or gallium atom, E5Indicate that phosphorus is former
Son or antimony atoms,
Y1~Y6The linking group of singly-bound or divalent is each independently represented,
R1~R16Each independently represent electron-withdrawing univalent perssad, R2And R3, be selected from R4~R6In at least two base
Group is selected from R7~R10In at least two group and be selected from R11~R16In at least two group can be mutually bonded shape respectively
Cyclization.
R1~R16Each independently represent electron-withdrawing univalent perssad.Electron-withdrawing univalent perssad refers to and hydrogen atom
It is more easily than the substituent group for attracting electronics from the atom side of bonding.R1~R16Preferably organic group.Organic group refers to tool
There is the atomic group of 1 or more carbon atom.For organic group, below equally.R2And R3, be selected from R4~R6In at least two base
Group is selected from R7~R10In at least two group and be selected from R11~R16In at least two group can be mutually bonded respectively.
The group of bonding can become cyclic annular.
As the example of electron-withdrawing univalent perssad, the halogen atoms such as fluorine atom, chlorine atom, bromine atom can be enumerated；Cyanogen
Base；Thiocyano；Nitro；The alkyl sulphonyls such as mesyl (such as carbon number is 1~12, preferably carbon number is 1~6)；Toluene sulphur
The aryl sulfonyls such as acyl group (such as carbon number is 6~18, preferably carbon number is 6~12)；The alkyl oxies sulphonyl such as methoxysulfonyl
Base (such as carbon number is 1~12, preferably carbon number is 1~6)；The aryloxies such as phenoxysulfonyl groups sulfonyl (such as carbon number be 6~
18, preferably carbon number is 6~12)；The acyl groups such as formoxyl, acetyl group, benzoyl (such as carbon number is 1~12, preferably carbon number is 1
~6)；The acyloxies such as formoxyl oxygroup, acetoxyl group (such as carbon number is 1~20, preferably carbon number is 1~6)；Methoxyl group carbonyl
The alkoxy carbonyls such as base, ethoxy carbonyl (such as carbon number is 2~10, preferably carbon number is 2~7)；Phenyloxycarbonyl, pyridyl group oxygen
Base carbonyl etc. " aryloxycarbonyl or heteroaryloxycarbonyl " (such as carbon number is 4~25, preferably carbon number is 5~15)；Trifluoro
Instead of " the halogen of halogen atom in the straight-chains such as methyl, pentafluoroethyl group, branched or cricoid " alkyl, alkenyl or alkynyl "
Alkyl, halogen alkenyl or alkynyl halide (such as carbon number is 1~10, preferably carbon number is 1~6)；In the aryl such as pentafluorophenyl group instead of
The halogen aryl (such as carbon number is 6~20, preferably carbon number is 6~12) of halogen atom；It is taken in the aryl alkyls such as pentafluorophenyl group methyl
For the halogen aryl alkyl of halogen atom (such as carbon number is 7~19, preferably carbon number is 7~13) etc..
In addition, aryl and heteroaryl are such as to Ra~RcAs illustrating.
In turn, the example as electron-withdrawing univalent perssad, from can make well negative electrical charge non-delocalized with efficiency
Viewpoint is set out, it is preferable to enumerate from the example of aforementioned electron-withdrawing univalent perssad " with hydrogen atom organic group " in
With halogen atom by hydrogen atom part or all instead of group.For example, perfluoroalkyl group sulfonyl, perfluor virtue can be enumerated
Base sulfonyl, perfluoroalkyl oxygroup sulfonyl, perfiuoroaryl oxygroup sulfonyl, perfluoro acidyl, perfluoro acidyl oxygroup, perfluoroalkoxy
Base carbonyl, perfiuoroaryl Epoxide carbonyl, perfluoroalkyl, perfluorinated alkenyl, perfluor alkynyl, perfiuoroaryl, perfiuoroaryl alkyl etc..
As the example of electron-withdrawing univalent perssad, the perfluor of straight-chain or branched that particularly preferred carbon number is 1~8
The perfiuoroaryl that the cyclic perfluoroalkyl group or carbon number that alkyl, carbon number are 3~6 are 6~18.
Electron-withdrawing univalent perssad is not limited to these.The example of electron-withdrawing univalent perssad illustrated above is also
It can have substituent group, can also have hetero atom.
As the example of electron-withdrawing univalent perssad, substituent group below can be specifically enumerated.
[chemical formula number 16]
Then, Y1~Y6Each independently represent the linking group of singly-bound or divalent.Y1~Y6When for singly-bound, refer to E and R
Direct Bonding.As the linking group of divalent, such as linker shown in any of following formula (1c)~(11c) being enumerated
Group.
[chemical formula number 17]
R each independently represents hydrogen atom or univalent perssad.
R is preferably organic group.The viewpoints such as the dissolubility of R from raising electron acceptor, in a solvent, more preferably respectively
It independently is alkyl, alkenyl, alkynyl, aryl or heteroaryl.These groups also can have substituent group, can also have miscellaneous original
Son.In addition, R is preferably electron-withdrawing univalent perssad, as electron-withdrawing univalent perssad, in addition to aforementioned electron-withdrawing one
Other than the example of valence group, such as it can also enumerate group shown in foregoing substituents group etc..
As anion, preferably negative electrical charge is predominantly located on oxygen atom, nitrogen-atoms, carbon atom, boron atom or gallium atom
Anion, the anion being more preferably located in oxygen atom, nitrogen-atoms, carbon atom or boron atom.Such as can enumerate formula (6b)~
Anion shown in any of (9b).Particularly preferred negative electrical charge is predominantly located at the anion in boron atom.
[chemical formula number 18]
R1~R10Each independently represent electron-withdrawing univalent perssad (R2And R3, be selected from R4~R6In at least two base
Roll into a ball and be selected from R7~R10In at least two group can also be mutually bonded respectively).
R1~R10Preferably organic group.As electron-withdrawing univalent perssad, aforementioned electron-withdrawing monovalence can be enumerated
Group shown in the example of group, foregoing substituents group etc., such as the preferably group shown in foregoing substituents group.Especially
Preferably containing the group of perfiuoroaryl.
[other any ingredients]
Charge-transporting material can also further contain dopant, charge-transporting low molecular compound, other charges
Transporting polymer etc..
[dopant]
Charge-transporting material can contain dopant.As long as dopant is by addition in hole transport ability polymer
The substance for showing doping effect, hole transport ability can be improved, is not particularly limited.Dopant can be used alone,
It can also be used in mixed way a variety of.Above-mentioned proton donor also can be used as dopant and function.
Dopant used in hole transport ability polymer is preferably the compound of electron acceptor, such as can enumerate Louis
Acid, Bronsted acid, transistion metal compound, ionic compound, halogen compounds, pi-conjugated based compound etc..Specifically, conduct
Lewis acid can enumerate FeCl3、PF5、AsF5、SbF5、BF5、BCl3、BBr3Deng；As Bronsted acid can enumerate HF, HCl, HBr,
HNO5、H2SO4、HClO4Equal inorganic acids, benzene sulfonic acid, p-methyl benzenesulfonic acid, dodecyl benzene sulfonic acid, polyvinylsulfonic acid, methanesulfonic acid,
The organic acids such as trifluoromethanesulfonic acid, trifluoroacetic acid, 1- fourth sulfonic acid, ethenylphenyl sulfonic acid, camphorsulfonic acid；As transition metal compound
Object can enumerate FeOCl, TiCl4、ZrCl4、HfCl4、NbF5、AlCl3、NbCl5、TaCl5、MoF5；As ionic compound, can lift
Four (pentafluorophenyl group) borate ions, three (trifluoromethane sulfonyl group) methide ions, bis- (trifluoromethane sulfonyl group) acyls are sub- out
Amine ion, hexafluoro-antimonic acid ion, AsF6 -(hexafluoro arsenic acid ion), BF4 -(tetrafluoro boric acid ion), PF6 -(hexafluorophosphate ion) etc.
Salt with perfluor anion, salt of conjugate base as anion with above-mentioned Bronsted acid etc.；As halogen compounds, can lift
Cl out2、Br2、I2、ICl、ICl3, IBr, IF etc.；As pi-conjugated based compound, TCNE (tetracyanoethylene), TCNQ can be enumerated
(four cyano quinone bismethane) etc..Furthermore it is also possible to use Japanese Unexamined Patent Publication 2000-36390 bulletin, Japanese Unexamined Patent Publication 2005-75948
Electron acceptor compound documented by number bulletin, Japanese Unexamined Patent Publication 2003-213002 bulletin etc..Preferably lewis acid, ion
Compound, pi-conjugated based compound etc.
[content]
The content of hole transport ability polymer with substituent group shown in formula (Ia) is from obtaining good hole transport ability
Viewpoint is set out, relative to the gross mass of hole transport ability material, preferably 50 mass % or more, more preferably 70 mass % with
Upper, further preferably 80 mass % or more.In addition, the content of the hole transport ability polymer with substituent group shown in formula (Ia)
From the viewpoint of the viewpoint for changing solubility fully and improving hole transport ability, relative to charge-transporting material
Gross mass, preferably 99.99 mass % or less, more preferably 99.9 mass % or less, further preferably 99.5 mass %
Below.
The content of proton donor goes out from the viewpoint for changing solubility fully and the viewpoint for improving hole transport ability
Preferably 0.01 mass % or more, hair is more preferably 0.1 mass % or more, is further excellent relative to hole transport ability polymer
It is selected as 0.5 mass % or more.In addition, from the viewpoint of keeping film forming well, it is excellent relative to hole transport ability polymer
It is selected as 50 mass % or less, more preferably 30 mass % or less, further preferably 20 mass % or less.
[method for making changes in solubility]
The reaction of leaving away of atomic group (A) can be carried out by heating, light irradiation etc., from the viewpoint of simple process,
It is preferred that heating.As long as heating temperature and time can make to leave away, reaction is sufficiently carried out, and is not particularly limited.It can also be with
Carry out both heating and light irradiation.
The heaters such as heating plate, baking oven can be used in heating.For temperature, from the viewpoint of being applicable in various substrates,
Preferably 300 DEG C or less, more preferably 250 DEG C or less, further preferably 230 DEG C or less.In addition, from reaction of leaving away is accelerated
Viewpoint is set out, and preferably 40 DEG C or more, more preferably 100 DEG C or more, further preferably 150 DEG C or more.Time gives birth to from raising
From the perspective of yield, preferably 2 hours or less, more preferably 1 hour or less, further preferably 30 minutes or less.In addition,
From the viewpoint of making to carry out with leaving away fully reacting, preferably 1 minute or more, more preferably 3 minutes or more, further preferred
It is 5 minutes or more.
Illumination, which is hit, can be used low pressure mercury lamp, medium pressure mercury lamp, high-pressure sodium lamp, ultrahigh pressure mercury lamp, metal halide lamp, xenon
The light sources such as lamp, fluorescent lamp, light emitting diode, sunlight.
< printing ink composition >
According to one embodiment, printing ink composition contains aforementioned charge-transporting material and can be by the charge-transporting
The organic solvent of material dissolution or dispersion.By using printing ink composition, this easy method can be easy by rubbing method
Ground forms organic layer.
(organic solvent)
Organic solvent is not particularly limited, such as can enumerate solvent usually used when coated polymeric.For example, can enumerate
Aliphatic alcohol, aliphatic hydrocarbon, aromatic hydrocarbon, fatty ether, aromatic ether, aliphatic ester, aromatic ester, amide, sulfoxide, ketone,
Organohalogen compound etc..
As aliphatic alcohol, preferably carbon number is 1~6 alcohol, such as can enumerate methanol, ethyl alcohol, isopropanol etc..
As aliphatic hydrocarbon, preferably carbon number be 5~10 alkane or carbon number be 5~10 cycloalkane, such as penta can be enumerated
Alkane, hexane, octane, hexamethylene etc..
As aromatic hydrocarbon, preferably carbon number is 6~13 aromatic hydrocarbon, such as can enumerate benzene,toluene,xylene, equal three
Toluene, tetrahydronaphthalene, diphenyl methane etc..
As fatty ether, such as ethylene glycol dimethyl ether, ethylene glycol Anaesthetie Ether, propylene glycol -1- monomethyl can be enumerated
Ether acetate etc..
As aromatic ether, such as 1,2- dimethoxy benzene, 1,3- dimethoxy benzene, anisole, phenetole, 2- can be enumerated
Methoxy toluene, 3- methoxy toluene, 4- methoxy toluene, 2,3- dimethyl anisole, 2,4- dimethyl anisole etc..
As aliphatic ester, such as ethyl acetate, n-butyl acetate, ethyl lactate, n-butyl lactate can be enumerated etc..
As aromatic ester, such as phenylacetate, phenyl propionate, methyl benzoate, ethyl benzoate, benzoic acid can be enumerated
Propyl ester, n-butylbenzoate etc..
As amide, such as n,N-Dimethylformamide, n,N-dimethylacetamide can be enumerated etc..
As sulfoxide, such as dimethyl sulfoxide, diethyl sulfoxide can be enumerated etc..
As ketone, such as tetrahydrofuran, acetone can be enumerated etc..
As organohalogen compound, such as chloroform, methylene chloride can be enumerated etc..
[content]
The content of organic solvent in printing ink composition, which can be considered, to be applicable in determine in various coating methods.For example,
The content of organic solvent is preferably to reach the amount of 0.1 mass % or more relative to the ratio of organic solvent, charge-transporting material,
The amount for more preferably reaching 0.2 mass % or more is further preferred that the amount for reaching 0.5 mass % or more.In addition, organic solvent
Content be preferably to reach 20 mass % amounts below relative to the ratio of organic solvent, charge-transporting material, more preferably
Reach 15 mass % amounts below, is further preferred that and reaches 10 mass % amounts below.
[additive]
Printing ink composition can also further contain additive as any ingredient.As additive, such as resistance can be enumerated
Poly- agent, stabilizer, tackifier, gelating agent, fire retardant, antioxidant, anti-reducing agent, oxidant, reducing agent, surface are modified
Agent, emulsifier, defoaming agent, dispersing agent, surfactant etc..
< organic layer >
According to one embodiment, organic layer is the layer formed using aforementioned charge-transporting material or printing ink composition.
In addition, according to one embodiment, the manufacturing method of organic layer includes: the work for being coated with the printing ink composition, forming coating layer
Sequence；With the process for carrying out heat treatment and/or photo-irradiation treatment to the coating layer.
By using printing ink composition, it can use rubbing method and form organic layer well.As coating method, such as can
Enumerate spin-coating method；The tape casting；Infusion process；Letterpress, intaglio printing, hectographic printing, lithographic printing, letterpress reverse graph
Brush, silk-screen printing, intaglio printing etc. have version printing method；Ink-jet method etc. is without method well known to version printing method etc..Utilize rubbing method shape
When at organic layer, can organic layer (coating layer) obtained is dry after it will be coated with using heating plate or baking oven, solvent is removed
It goes.
By being heated to the organic layer (coating layer) after coating, light irradiation etc. processing, atomic group (A) can be made from sky
It leaves away in the transporting polymer of cave, the solubility of organic layer (coating layer) is made to change.For example, by changing solubility
Organic layer on other organic layers are laminated, can easily seek the multiple stratification of organic electronic element.Change solubility has
Contain the hole transport ability polymer with the group, such as tolyl that generate after atomic group (A) is left away in machine layer.
It is preferable to use the printing ink compositions containing organic solvent in the formation on upper layer.As organic solvent, can be used aforementioned
Organic solvent, such as the hole transport ability polymer contained in the lower layer contains the parent to nonpolar solvent or low polar solvent
With property when high atomic group (A), the nonpolar solvent or low polar solvent can be used.
The thickness of the organic layer after solubility is changed from the viewpoint of improving charge transfer efficiency, preferably
0.1nm or more, more preferably 1nm or more, further preferably 3nm or more.In addition, sight of the thickness of organic layer from reduction resistance
Point sets out, preferably 300nm or less, more preferably 200nm or less, further preferably 100nm or less.
< organic electronic element >
According to one embodiment, organic electronic element at least has aforementioned organic layer.In addition, according to an embodiment party
The manufacturing method of formula, organic electronic element includes: the process of coating printing ink composition, formation coating layer；With to the coating layer
The process for carrying out heat treatment and/or photo-irradiation treatment, formation organic layer.As organic electronic element, such as can enumerate organic
EL element, organic photoelectric converter, organic transistor etc..Organic electronic element preferably has matches between at least 1 pair of electrode
It is equipped with the structure of organic layer.
[organic EL element]
According to one embodiment, organic EL element at least has aforementioned organic layer.In addition, according to one embodiment,
The manufacturing method of organic EL element includes: the process of coating printing ink composition, formation coating layer；Add with to the coating layer
The process of heat treatment and/or photo-irradiation treatment, formation organic layer.Organic EL element is generally configured with luminescent layer, anode, cathode and base
Plate has other functional layers such as hole injection layer, electron injecting layer, hole transmission layer, electron transfer layer as needed.Each layer can
To be formed using vapour deposition method, it also can use rubbing method and formed.Organic EL element preferably have organic layer as luminescent layer or its
Its functional layer more preferably has organic layer as functional layer, further preferably has organic layer as hole injection layer and hole
At least one party in transport layer.
Fig. 1 is the schematic cross-section for indicating an embodiment of organic EL element.The organic EL element of Fig. 1 is multilayer knot
The element of structure has substrate 8 in order, anode 2, the hole injection layer 3 formed by aforementioned organic layer, hole transmission layer 6, shines
Layer 1, electron transfer layer 7, electron injecting layer 5 and cathode 4.Each layer is illustrated below.
[luminescent layer]
As material used in luminescent layer, the luminous material such as low molecular compound, polymer, dendrimer can be used
Material.Polymer is since dissolubility in a solvent is high, is suitable for rubbing method, preferably.As luminescent material, phosphor can be enumerated
Material, phosphor material, thermal activation delayed fluorescence material (TADF) etc..
As fluorescent material, can enumerate perylene, cumarin, rubrene, quinacridone, Stilbene, dye laser pigment,
Aluminium complex, their low molecular compounds such as derivative；Polyfluorene, polyhenylene, polyphenylene vinylene, polyvinyl click
Azoles, fluorenes-diazosulfide copolymer, fluorenes-triphenylamine copolymer, their polymer such as derivative；Their mixture etc..
As phosphor material, the metal complex etc. containing metals such as Ir, Pt can be used.As Ir ligand compound
Object, such as FIr (pic) (bis- [(4,6- difluorophenyl)-pyridine-N, C for carrying out blue-light-emitting can be enumerated2] pyridine carboxylic acid conjunction iridium
(III)) Ir (ppy) of green emitting, is carried out3(three (2- phenylpyridines) close iridium), (btp) for carrying out emitting red light2Ir(acac)
(bis- (2- (2 '-benzos [4,5- α] thienyl) pyridine-N, C3) (acetylacetone,2,4-pentanedione) iridium), Ir (piq)3(three (1- phenyl isoquinolin quinolines)
Iridium) etc..As Pt complex, such as PtOEP (2,3,7,8,12,13,17,18- eight second for carrying out emitting red light can be enumerated
Base -21H, 23H- porphyrin platinum) etc..
When luminescent layer contains phosphor material, other than phosphor material, preferably further contain material of main part.As main body
Low molecular compound, polymer or dendrimer can be used in material.As low molecular compound, such as CBP can be enumerated
(4,4 '-bis- (9H- carbazole -9- base) biphenyl), mCP (bis- (9- carbazyl) benzene of 1,3-), CDBP (4,4 '-bis- (carbazole -9- bases) -
2,2 '-dimethyl diphenyls), their derivative etc., as polymer, aforementioned organic electronic material, polyvinyl click can be enumerated
Azoles, polyhenylene, polyfluorene, their derivative etc..
As thermal activation delayed fluorescence material, such as Adv.Mater. can be enumerated, 21,4802-4906 (2009)；
Appl.Phys.Lett.,98,083302(2011)；Chem.Comm.,48,9580(2012)；Appl.Phys.Lett.,101,
093306(2012)；J.Am.Chem.Soc.,134,14706(2012)；Chem.Comm.,48,11392(2012)；Nature,
492,234(2012)；Adv.Mater.,25,3319(2013)；J.Phys.Chem.A,117,5607(2013)；
Phys.Chem.Chem.Phys.,15,15850(2013)；Chem.Comm.,49,10385(2013)；Chem.Lett.,43,
The compound recorded in 319 (2014) etc..
[hole transmission layer, hole injection layer]
As material used in hole transmission layer and hole injection layer, aforementioned charge-transporting material can be enumerated.In addition,
As material used in hole injection layer and hole transmission layer, the hole transport without group shown in formula (Ia) can be enumerated
Property polymer.Other than not having group shown in formula (Ia), can have has with above-mentioned the hole transport ability polymer
The identical structure of hole transport ability polymer of group shown in formula (Ia).That is, not having the hole of group shown in formula (Ia)
Transporting polymer is for example with structural unit L, structural unit T and/or structural unit B.
In turn, as well known material, such as aromatic amine based compound (such as N, N '-two (naphthalene -1- base)-can be enumerated
The aromatic diamines such as N, N '-diphenyl-benzidine (α-NPD)), phthalocyanine based compound, thiophene based compound (such as poly- (3,4-
Ethylenedioxy thiophene): the thiophene system electric conductive polymer such as poly- (4- styrene sulfonate) (PEDOT:PSS)) etc..
[electron transfer layer, electron injecting layer]
As material used in electron transfer layer and electron injecting layer, such as phenanthroline derivative, bipyridyl can be enumerated
The fused rings such as derivative, nitro-substituted fluorene derivative, diphenylquinone derivatives, thiopyrandioxide derivatives, naphthalene, perylene
Tetracarboxylic anhydride, carbon imidodicarbonic diamide, fluorenes fork methane Derivatives, anthraquinone bismethane and anthracyclinone derivatives, oxadiazole derivatives, thiadiazoles
Derivative, benzimidizole derivatives, quinoxaline derivant, aluminium complex etc..In addition, aforementioned organic electronic material can also be with
It uses.
[cathode]
It is closed as cathode material, such as using the metals such as Li, Ca, Mg, Al, In, Cs, Ba, Mg/Ag, LiF, CsF or metal
Gold.
[anode]
As anode material, such as use metal (such as Au) or conductive other materials.As other materials,
Such as oxide (such as ITO: indium oxide/tin oxide), electroconductive polymer (such as polythiophene-polystyrolsulfon acid can be enumerated
Mixture (PEDOT:PSS)).
[substrate]
As substrate, glass, plastics etc. can be used.Substrate is preferably transparent, it is additionally preferred to have flexibility.It is preferred that making
With quartz glass, translucent resin film etc..
As resin film, such as can enumerate by polyethylene terephthalate, polyethylene naphthalate, polyethers
Sulfone, polyetherimide, polyether-ether-ketone, polyphenylene sulfide, polyarylate, polyimides, polycarbonate, Triafol T, acetic acid third
The film of the formation such as acid cellulose.
When using resin film, in order to inhibit the transmission of water vapour, oxygen etc., silica, nitrogen can also be coated on resin film
Carried out after the inorganic matters such as SiClx using.
[illuminant colour]
The illuminant colour of organic EL element is not particularly limited.White organic EL element due to can be used for it is home-use illumination,
In the various luminaires such as the backlight of room light, wrist-watch or liquid crystal, therefore preferably.
As the method for forming white organic EL unit, it can use using multiple luminescent materials, keep multiple illuminant colours same
Shi Faguang and method by its colour mixture.It as the combination of multiple illuminant colours, is not particularly limited, can enumerate containing blue, green
And the combination of 3 red luminous maximum wavelengths, contain blue and yellow, yellow green and 2 luminous maximum wavelengths such as orange
Combination etc..The control of illuminant colour can be carried out by the adjustment of the type and amount of luminescent material.
< display element, lighting device, display device >
According to one embodiment, display element has aforementioned organic EL element.Such as made by using organic EL element
For element corresponding with red, green and blue (RGB) each pixel, colored display element can get.In the forming method of image, have
The simple matrix type that each organic EL element being arranged on panel is directly driven using rectangular electrode is configured to；
With the active array type that configuration thin film transistor (TFT) is driven in each element.
In addition, according to one embodiment, lighting device has aforementioned organic EL element.In turn, according to an embodiment party
Formula, display device have aforementioned illumination apparatus and the liquid crystal cell as display means.Such as display device can be as back
Light uses aforementioned illumination apparatus, uses the display device of known liquid crystal cell, i.e. liquid crystal display device as display means.
Embodiment
Embodiments of the present invention are specifically described by the following examples.Embodiments of the present invention be not limited to
Under embodiment.
The synthesis > of < hole transport ability polymer
(preparation of Pd catalyst)
In glove box in a nitrogen environment, three (two benzylideneacetones) two palladiums are weighed in sample cell at room temperature
(73.2mg, 80 μm of ol) add anisole (15ml) and stir 30 minutes.Equally, tri-tert-butylphosphine is weighed in sample cell
(129.6mg, 640 μm of ol) add anisole (5mL) and stir 5 minutes.These solution are mixed, are stirred at room temperature 30 points
Catalyst is made in clock.Whole solvents are reused after being de-gassed by 30 minutes or more nitrogen bubblings.
(synthesis that the hole transport ability polymer 1 of group shown in formula (Ia) is contained in end)
Following monomer L (5.0mmol), following monomer B (2.0mmol), following monomer T1 are added in three neck round bottom flask
(4.0mmol) and anisole (20mL), and then add prepared Pd catalyst solution (7.5mL).After stirring 30 minutes, add
Add 10% tetraethyl ammonium hydroxide aqueous solution (20mL).Whole solvents are de-gassed by 30 minutes or more nitrogen bubblings
After reuse.Resulting mixture is heated to reflux 2 hours.All operationss so far carry out under stream of nitrogen gas.
[chemical formula number 19]
Organic layer is washed after reaction, organic layer is injected into methanol-water (9:1).To generated heavy
It forms sediment and is recycled by filtering, washed with methanol-water (9:1).Resulting precipitating is dissolved in toluene, from methanol again
Precipitating.It is recycled, is dissolved in toluene using filtering to precipitate gained, add metal absorbent (Strem Chemicals corporation
" Triphenylphosphine, polymer-bound on styrene-divinylbenzene copolymer ", relative to
Sediment 100mg is 200mg) and stir an evening.After stirring, metal absorbent and insoluble matter are filtered to remove, utilize rotation
Turn evaporimeter filtrate is concentrated.After concentrate is dissolved in toluene, the reprecipitation from methanol-acetone (8:3).It will using filtering
Generated precipitating recycling, is washed using methanol-acetone (8:3).Gained precipitating is dried in vacuo, hole is obtained and passes
Defeated property polymer 1.The number-average molecular weight of gained hole transport ability polymer 1 is 15,900, weight average molecular weight 41,600.
Number-average molecular weight and weight average molecular weight use the GPC (polystyrene conversion) of tetrahydrofuran (THF) by eluent
It is measured.Determination condition is as follows.
Liquid-feeding pump: L-6050 Co., Ltd. Hitachi High-Technologies
UV-Vis detector: L-3000 Co., Ltd. Hitachi High-Technologies
Chromatographic column: Gelpack (registered trademark) GL-A160S/GL-A150S Hitachi Chemical Co., Ltd.
Eluent: THF (HPLC is used, is free of stabilizer) Wako Pure Chemical Industries, Ltd.
Flow velocity: 1mL/min
Column temperature: room temperature
Molecular weight standard substance: standard polystyren
(synthesis that the hole transport ability polymer 2 of group shown in formula (Ia) is contained in end)
Following monomer L (5.0mmol), following monomer B (2.0mmol), following monomer T2 are added in three neck round bottom flask
(4.0mmol) and anisole (20mL), and then add prepared Pd catalyst solution (7.5mL).Later and hole transport ability
The synthesis of polymer 1 is carried out similarly, and synthesizes hole transport ability polymer 2.The equal molecule of number of gained hole transport ability polymer 2
Amount is 20,200, weight average molecular weight 69,000.
[chemical formula number 20]
(synthesis of the hole transport ability polymer 3 without group shown in formula (Ia))
Following monomer L (5.0mmol), following monomer B (2.0mmol), following monomer T3 are added in three neck round bottom flask
(4.0mmol) and anisole (20mL), and then add prepared Pd catalyst solution (7.5mL).Later and hole transport ability
The synthesis of polymer 1 is carried out similarly, and synthesizes hole transport ability polymer 3.The equal molecule of number of gained hole transport ability polymer 3
Amount is 15,800, weight average molecular weight 141,100.
[chemical formula number 21]
The evaluation > of the changes in solubility of < charge-transporting material
[embodiment 1]
Hole transport ability polymer 1 (10.0mg) is dissolved in toluene (1,991 μ L), polymer solution is obtained.In addition,
Following salt (0.309mg) are dissolved in toluene (309 μ L), salting liquid is obtained.By resulting polymer solution and salt
Solution mixing, preparation coating solution (printing ink composition containing charge-transporting material).With revolving speed 3 under room temperature (25 DEG C),
000min-1Coating solution is spin-coated on quartz glass plate, organic film is formed.Then, on hot plate, 180 DEG C, 10 minutes
Under conditions of quartz glass plate is heated.Later, quartz glass clamped using pincet, be immersed in and fill toluene (25
DEG C) 200mL beaker in, by quartz glass plate on the thickness direction of quartz glass plate, internal vibration in 10 seconds 10 back and forth.
By the ratio between absorbance (Abs) of absorption maximum (λ max) in the UV-vis spectrum of the organic film of dipping front and back, utilize following formula
Find out the residual film ratio of organic film.Residual film ratio is higher, it can be said that the changes in solubility of charge-transporting material is bigger.
[chemical formula number 22]
[mathematical expression 1]
The absorbance of Abs × 100 of organic film before the Abs/ dipping of organic film after residual film ratio (%)=dipping
Measurement is to measure 300~500nm wavelength using spectrophotometer (Hitachi Co., Ltd U-3310), to organic film
The absorbance under maximum absorption wavelength in range.
In addition, being measured in the same manner as described above charge-transporting material other than making 180 DEG C, 30 minutes of heating condition
Changes in solubility evaluation.
[embodiment 2]
Hole transport ability polymer 1 (10.0mg) is dissolved in toluene (1,189 μ L), polymer solution is obtained.In addition,
Above-mentioned salt (1.01mg) is dissolved in toluene (1,111 μ L), salting liquid is obtained.By resulting polymer solution and salt
Solution mixing, preparation coating solution (printing ink composition containing charge-transporting material).With revolving speed 3 under room temperature (25 DEG C),
000min-1Coating solution is spin-coated on quartz glass plate, organic film is formed.Then, charge is carried out similarly to Example 1
The evaluation of the changes in solubility of transporting material.
[embodiment 3]
Hole transport ability polymer 2 (10.0mg) is dissolved in toluene (1,991 μ L), polymer solution is obtained.In addition,
Above-mentioned salt (0.309mg) is dissolved in toluene (309 μ L), salting liquid is obtained.By resulting polymer solution and salt
Solution mixing, preparation coating solution (printing ink composition containing charge-transporting material).With revolving speed 3 under room temperature (25 DEG C),
000min-1Coating solution is spin-coated on quartz glass plate, organic film is formed.Then, charge is carried out similarly to Example 1
The evaluation of the changes in solubility of transporting material.
[comparative example 1]
Hole transport ability polymer 1 (10.0mg) is dissolved in toluene (2,301 μ L), polymer solution is obtained.In room
With revolving speed 3,000min under warm (25 DEG C)-1Resulting polymer solution (printing ink composition) is spin-coated on quartz glass plate, shape
At organic film.Then, the evaluation of the changes in solubility of hole transport ability polymer is carried out similarly to Example 1.
[comparative example 2]
Hole transport ability polymer 3 (10.0mg) is dissolved in toluene (1,991 μ L), polymer solution is obtained.In addition,
Above-mentioned salt (0.309mg) is dissolved in toluene (309 μ L), salting liquid is obtained.By resulting polymer solution and salt
Solution mixing, preparation coating solution (printing ink composition).With revolving speed 3,000min under room temperature (25 DEG C)-1Solution spin coating will be coated with
On quartz glass plate, organic film is formed.Then, the solubility for carrying out charge-transporting material similarly to Example 1 becomes
The evaluation of change.
[comparative example 3]
Hole transport ability polymer 3 (10.0mg) is dissolved in toluene (1,189 μ L), polymer solution is obtained.In addition,
Above-mentioned salt (1.01mg) is dissolved in toluene (1,111 μ L), salting liquid is obtained.By resulting polymer solution and salt
Solution mixing, preparation coating solution (printing ink composition).With revolving speed 3,000min under room temperature (25 DEG C)-1Solution spin coating will be coated with
On quartz glass plate, organic film is formed.Then, the solubility for carrying out charge-transporting material similarly to Example 1 becomes
The evaluation of change.
By Examples 1 to 3 and comparative example 1~3 evaluation result is shown in table 1.
Table 1
* 1: the concentration on the basis of the quality of printing ink composition
* 2: the concentration on the basis of the quality of hole transport ability polymer
By using containing with the hole transport ability polymer of group and the charge of proton donor shown in formula (Ia)
The solubility of transporting material, hole transport ability polymer is changed.By the charge-transporting material of Examples 1 to 3,
Obtain high residual film ratio.On the other hand, the charge-transporting material without proton donor (comparative example 1) and hole transport ability
Polymer does not have in the charge-transporting material (comparative example 2 and 3) of group shown in formula (Ia), is the low result of residual film ratio.
The dissolubility variation of the hole transport ability polymer of Examples 1 to 3 is considered by the oxygen from monomer T1 or T2
Caused by the cleacvage reaction of methylene.That is, proton donor is mixed in hole transport ability polymer, by being heated,
Atomic group (A) is left away, and group shown in formula (Ia) becomes tolyl, is changed to the compatibility of organic solvent.Its result
It can speculate the variation that hole transport ability polymer has occurred to the solubility of organic solvent.In Examples 1 to 3, sky has occurred
Reduction of the cave transporting polymer to the solubility of toluene, and then the residual film ratio of organic layer increases.
The production > of < organic EL element
[embodiment 4]
Hole transport ability polymer 1 (10.0mg), above-mentioned salt (0.5mg) and toluene (2.3mL) are mixed, ink is prepared
Composition 1.In a nitrogen environment, on the glass substrate for having ITO with 1.6mm width Butut, with revolving speed 3,000min-1Spin coating oil
It after ink composition 1, heats 10 minutes, is formed hole injection layer (30nm) on hot plate, at 210 DEG C.
Then, hole transport ability polymer 3 (20.0mg) and toluene (2.3mL) are mixed, prepares printing ink composition 2.?
On above-mentioned hole injection layer, with revolving speed 3,000min-1Spin coating printing ink composition 2 heats 10 minutes on hot plate, at 200 DEG C
It makes it dry, is formed hole transmission layer (40nm).Hole transmission layer is formd in the case where dissolving hole injection layer.
Later, glass substrate is moved in vacuum evaporation plating machine, is formed a film in order CBP with vapour deposition method on the hole transport layer:
Ir(ppy)3(94:6,30nm), BAlq (10nm), Alq3(30nm), LiF (0.8nm) and Al (100nm), are sealed processing,
Organic EL element is made.
[embodiment 5]
Other than hole transport ability polymer 1 is substituted for hole transport ability polymer 2, make similarly to Example 4
Organic EL element is made.
[comparative example 4]
Other than hole transport ability polymer 1 is substituted for hole transport ability polymer 3, make similarly to Example 4
Organic EL element is made.In the formation of hole transmission layer, hole injection layer dissolves, and fails to form multilayered structure.
When the organic EL element obtained in embodiment 4, embodiment 5 and comparative example 4 applies voltage, green hair is confirmed
Light.Light emission luminance 1,000cd/m is measured to each element2When driving voltage and luminous efficiency and original intensity 3,
000cd/m2Under luminescent lifetime (brightness half-life).Measurement result is shown in table 2.
Table 2
In the organic EL element of embodiment 4 and 5, by the organic layer containing excellent solvent resistance, multilayered structure is formd.
Organic EL element of the organic EL element of embodiment 4 and 5 relative to comparative example 4, obtains longer luminescent lifetime.
The effect of embodiments of the present invention is shown above by embodiment.In addition, in addition to sky used in embodiment
Other than the transporting polymer of cave, organic electronic can also be carried out by above explained hole transport ability polymer and proton donor
The multiple stratification of element, resulting organic electronic element show same excellent effect.
Symbol description
1 luminescent layer
2 anodes
3 hole injection layers
4 cathodes
5 electron injecting layers
6 hole transmission layers
7 electron transfer layers
8 substrates
Claims (16)
1. a kind of charge-transporting material contains hole transport ability polymer and matter with group shown in following formula (Ia)
Sub- donor,
[chemical formula number 1]
In formula (Ia), A indicates that the organic group of monovalence, R each independently represent the substituent group of monovalence, and m indicates 1~3 integer,
N indicates that 0~4 integer, m+n are 5 or less.
2. charge-transporting material according to claim 1, wherein group shown in the formula (Ia) contains following formula
(Ib) group shown in,
[chemical formula number 2]
In formula (Ib), A indicates that the organic group of monovalence, R each independently represent the substituent group of monovalence, and n indicates 0~4 integer.
3. charge-transporting material according to claim 1 or 2, wherein the proton donor contains following formula (II)s
Compound represented,
[chemical formula number 3]
In formula (II), Ra~RcHydrogen atom, alkyl, aryl alkyl, aryl or heteroaryl are each independently represented, R is selected froma~Rc
In at least two group can be mutually bonded to form ring；
A indicates anion.
4. charge-transporting material described in any one of claim 1 to 3, wherein the hole transport ability polymer
With branched structure.
5. charge-transporting material according to any one of claims 1 to 4, wherein the hole transport ability polymer
With at least one kind of in aromatic amine structure and carbazole structure.
6. charge-transporting material according to any one of claims 1 to 5, wherein the hole transport ability polymer
There is group shown in the formula (Ia) at least one end.
7. a kind of printing ink composition contains charge-transporting material according to any one of claims 1 to 6 and solvent.
8. a kind of organic layer is formed using charge-transporting material described in any one of claim 1~6.
9. a kind of organic electronic element, with organic layer according to any one of claims 8.
10. a kind of organic electroluminescent device, with organic layer according to any one of claims 8.
11. a kind of display element has organic electroluminescent device described in any one of claim 10.
12. a kind of lighting device has organic electroluminescent device described in any one of claim 10.
13. a kind of display device has lighting device described in claim 12 and the liquid crystal cell as display means.
14. a kind of manufacturing method of organic layer, it includes:
The process for being coated with printing ink composition as claimed in claim 7, forming coating layer；With
Apply the process of at least one kind of processing in heat treatment and photo-irradiation treatment to the coating layer.
15. a kind of manufacturing method of organic electronic element, it includes:
The process for being coated with printing ink composition as claimed in claim 7, forming coating layer；With
The process that at least one kind of processing in heat treatment and photo-irradiation treatment is applied to the coating layer, forms organic layer.
16. a kind of manufacturing method of organic electroluminescent device, it includes:
The process for being coated with printing ink composition as claimed in claim 7, forming coating layer；With
The process that at least one kind of processing in heat treatment and photo-irradiation treatment is applied to the coating layer, forms organic layer.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016164723 | 2016-08-25 | ||
| JP2016-164723 | 2016-08-25 | ||
| PCT/JP2017/026860 WO2018037813A1 (en) | 2016-08-25 | 2017-07-25 | Charge transport material, ink composition and organic electronic element |
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| US (1) | US20190229268A1 (en) |
| JP (1) | JP6915621B2 (en) |
| KR (1) | KR20190042595A (en) |
| CN (1) | CN109643765A (en) |
| DE (1) | DE112017004204T5 (en) |
| TW (1) | TWI753932B (en) |
| WO (1) | WO2018037813A1 (en) |
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| CN102449799A (en) * | 2009-06-01 | 2012-05-09 | 日立化成工业株式会社 | Organic electronic material, ink composition containing same, and organic thin film, organic electronic element, organic electroluminescent element, lighting device, and display device formed therewith |
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| JP4608317B2 (en) * | 2002-11-01 | 2011-01-12 | ジョージア・テック・リサーチ・コーポレーション | Sacrificial composition, method of use thereof, and method of decomposition thereof |
| JP4186758B2 (en) | 2003-09-01 | 2008-11-26 | 三菱化学株式会社 | Polymer compound, hole injecting / transporting material, organic electroluminescent device material and organic electroluminescent device |
| JP2006279007A (en) | 2005-03-02 | 2006-10-12 | Konica Minolta Holdings Inc | Organic electroluminescent element, display device, and lighting device |
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| JP6252829B2 (en) * | 2013-07-12 | 2017-12-27 | 凸版印刷株式会社 | CHARGE TRANSPORT POLYMER, AND CHARGE TRANSPORT POLYMER COMPOSITION, LIGHT-EMITTING CHARGE TRANSPORT FILM, AND ORGANIC EL DEVICE |
| JP6467999B2 (en) | 2015-03-06 | 2019-02-13 | 富士ゼロックス株式会社 | Information processing system and program |
-
2017
- 2017-07-25 US US16/327,105 patent/US20190229268A1/en not_active Abandoned
- 2017-07-25 KR KR1020197006319A patent/KR20190042595A/en not_active Application Discontinuation
- 2017-07-25 JP JP2018535545A patent/JP6915621B2/en active Active
- 2017-07-25 WO PCT/JP2017/026860 patent/WO2018037813A1/en active Application Filing
- 2017-07-25 CN CN201780051373.3A patent/CN109643765A/en active Pending
- 2017-07-25 DE DE112017004204.6T patent/DE112017004204T5/en not_active Withdrawn
- 2017-08-01 TW TW106125835A patent/TWI753932B/en active
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|---|---|---|---|---|
| JP2007257897A (en) * | 2006-03-20 | 2007-10-04 | Seiko Epson Corp | LIGHT EMITTING DEVICE MANUFACTURING METHOD, LIGHT EMITTING DEVICE MANUFACTURING METHOD, AND ELECTRONIC DEVICE MANUFACTURING METHOD |
| CN102449799A (en) * | 2009-06-01 | 2012-05-09 | 日立化成工业株式会社 | Organic electronic material, ink composition containing same, and organic thin film, organic electronic element, organic electroluminescent element, lighting device, and display device formed therewith |
| WO2013096921A1 (en) * | 2011-12-22 | 2013-06-27 | Georgia Tech Research Corporation | Non-crosslinked polystyrene triscarbazole hole transport materials |
| JP2015159077A (en) * | 2014-02-25 | 2015-09-03 | 日立化成株式会社 | Method for manufacturing organic electronic device |
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| WO2018037813A1 (en) | 2018-03-01 |
| TW201821592A (en) | 2018-06-16 |
| JPWO2018037813A1 (en) | 2019-08-08 |
| TWI753932B (en) | 2022-02-01 |
| JP6915621B2 (en) | 2021-08-04 |
| KR20190042595A (en) | 2019-04-24 |
| US20190229268A1 (en) | 2019-07-25 |
| DE112017004204T5 (en) | 2019-05-29 |
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